“There is no one who knows more, and can teach legal writing better, than Susan McCloskey. Her teaching style is both hugely informative and delightful.”
— Albert M. Rosenblatt, Judge, New York Court of Appeals, Retired

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Why Do Writers Bother with Outlines?

In sixth-grade English class, Sister Mary Rose taught her pupils to create formal outlines. She described how our next assignment was sure to generate in each of us a host of thoughts. Those thoughts would then take their places in flush-left or variously indented rows, some preceded by Roman numerals, some by capital letters, others by Arabic numerals, and still others by lowercase letters. That outline would then lead irresistibly to what she called a theme. She enjoined us to carry out this perfectly rational procedure for everything we wrote.

This regimen persisted until Sister Mary Rose judged that the words, “Class, your next theme will be . . . ” had the power to marshal at each pupil’s desk, with Pavlovian regularity, a phalanx of numerals and letters poised to overwhelm any pleasure her young charges might take in the act of writing.

My reaction to Sister Mary Rose’s teaching made me no fan of formal outlines. I know writers who swear by them, insisting that a thorough outline makes the first draft a snap to produce and drains the anxiety from even a pressing deadline. But I am, at best, an informal outliner. I prepare to write by doing my research and then taking the essential steps of defining precisely what my purpose is and what my intended readers want, need, and expect. Then I make a quick list of the points I need to make and put them in what seems a workable order. Then I start writing, knowing that my first draft will bear a family resemblance to my outline, though probably that of a cousin rather than an identical twin.

Most of the writers I work with favor this looser, less formal approach to preparing to write. Whether they’re drafting a contract or a legal brief, a marketing proposal or a lab report, they understand writing as a creative process. They want a path through the terrain they plan to enter, but they also want the new ideas, unforeseen connections, and genuine insights that the creative act of writing can bring. A map that shows every entrance and exit, every mile marker, every rest stop or fast-food outlet along the way has less to offer them than a pirate’s map, with a few squiggles distinguishing land from sea and a bold X marking the spot of the buried treasure.

Formal and informal outliners alike believe that Fortune favors the prepared mind. They disagree only about how meticulous the preparation should be. They have more in common with each other than with the adventurous souls who set out blindfolded on a writing project, feeling their way from sentence to sentence, paragraph to paragraph, busily skirting a pitfall here only to run headlong into a wall there. Without even the guidance of a well-formulated purpose and a lively sense of their intended reader, let alone any kind of outline, these writers are ill-equipped to meet a deadline, and they leave the quality of their product entirely to chance.

Those who fall in this devil-may-care category and those who outline informally can profit from what I call an after-the-fact outline, one created after the first draft is done. It’s an outline of the draft the writer has actually produced, not the one he or she had planned to produce. Simply number the paragraphs, write the numbers in the margin, and summarize the focus of each paragraph in a phrase or a clause on the appropriate line.

The act of making the outline is revealing in itself. A hard-to-summarize paragraph turns out to be two or more paragraphs inadvertently merged into one. A paragraph with a single focus calls out for a good topic sentence to express it. Flag the passage and then return to the draft to repair it.

Once this digest of the draft is complete, the writer can easily see the structure of a document. It’s suddenly clear that paragraph 6, say, would be better placed after paragraph 13, or that paragraphs 19 and 11 unnecessarily make the same point. That important shift in direction after paragraph 9 needs to be marked by a stronger transition. Once the structure falls into place, the writer can also see where to provide headings to guide the reader through the material.

Because my initial outline is only provisional, I have come to rely on the after-the-fact outline as a fast and easy way to check both the content and structure of anything I write longer than a page or two. My clients have also made inventive use of it, using it to coordinate parts of a document drafted by several writers or to outline an opponent’s argument that they will counter in a court of law, on the op-ed page, or in a policy blog.

So Sister Mary Rose may have been on to something when she insisted that her pupils submit an outline for every assignment we wrote. I wonder how many of us wrote our papers and then outlined them? I suspect there were many of us, trying with all our sixth-grade might to carve out a zone of freedom amid those bristling numbers and letters, to protect for the act of writing an element of surprise.